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Middleway Holiday Rentals

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Check prices for these dates

In two weeks
4 Sept - 6 Sept
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

Our top choices for Middleway holiday rentals

Exterior

1. Custom Train-Themed Lodge on 7 Private Acres with Walking Trails

Custom Train-Themed Lodge on 7 Private Acres with Walking Trails
Martinsburg
9.8 out of 10, Exceptional, (24 reviews)
"Nice place to stay. Could use some privacy."
United States
Arnold A.
The price is HK$671
HK$2,055 total
includes taxes & fees
24 Aug - 25 Aug
Custom Train-Themed Lodge on 7 Private Acres with Walking Trails
Exterior

2. ❤️ Secluded 1940s Romantic Tiny House on the River

❤️ Secluded 1940s Romantic Tiny House on the River
Shepherdstown
9.8 out of 10, Exceptional, (82 reviews)
"Enjoyed my stay I appreciate the view and Rich. "
United States
Joseph
The price is HK$508
HK$1,043 total
includes taxes & fees
31 Aug - 1 Sept
❤️ Secluded 1940s Romantic Tiny House on the River
Dining

3. Quaint Mini Cottage in Shepherdstown - Walking Distance

Quaint Mini Cottage in Shepherdstown - Walking Distance
Shepherdstown
9.8 out of 10, Exceptional, (23 reviews)
"Host let us in a bit early which was nice!"
United States
John
The price is HK$941
HK$1,745 total
includes taxes & fees
23 Aug - 24 Aug
Quaint Mini Cottage in Shepherdstown - Walking Distance
Outdoor spa tub

4. Cottage w/ Hot Tub and 100-Mile Valley Views!

Cottage w/ Hot Tub and 100-Mile Valley Views!
Harpers Ferry
9.8 out of 10, Exceptional, (26 reviews)
"We enjoyed our stay and the property was exactly what we were looking for in a mountain getaway peaceful, private, and immersed in the woods with beautiful views and a relaxing atmosphere.The home was clean, quiet, and met our needs well for a restful escape. The hosts were communicative and supportive, although we did not need to reach out during our stay.The driveway is definitely mountain-style, so guests should come prepared and be mindful of the vehicle they bring, but the secluded setting...
United States
B S.
The price is HK$784
HK$2,910 total
includes taxes & fees
31 Aug - 1 Sept
Cottage w/ Hot Tub and 100-Mile Valley Views!
Smart TV

5. Wolf Den - Airy Cabin w/ Hot Tub & Valley Views!

Wolf Den - Airy Cabin w/ Hot Tub & Valley Views!
Harpers Ferry
9.8 out of 10, Exceptional, (19 reviews)
"We had a wonderful stay. The communication and the guestbook were wonderful. The view was gorgeous and the property was clean and comfortable. "
United States
Kaitlyn C.
The price is HK$784
HK$3,106 total
includes taxes & fees
24 Aug - 25 Aug
Wolf Den - Airy Cabin w/ Hot Tub & Valley Views!
Outdoor spa tub

6. The Blue Jay | New House in the Woods w/ Hot Tub

The Blue Jay | New House in the Woods w/ Hot Tub
Harpers Ferry
10.0 out of 10, Exceptional, (4 reviews)
"Great place. Very well stocked house everything you need Great response from host. Very nice place. Road is a little rough as explained in listing "
United States
Brett D.
The price is HK$784
HK$2,904 total
includes taxes & fees
3 Sept - 4 Sept
The Blue Jay | New House in the Woods w/ Hot Tub
TV, fireplace, offices

7. Fireplace, Wraparound Deck, & WiFi at Chalet Cabin

Fireplace, Wraparound Deck, & WiFi at Chalet Cabin
Gerrardstown
8.2 out of 10, Very good, (19 reviews)
"Nice relaxing place. Enjoyed it very much."
United States
Scott K.
The price is HK$1,069
HK$2,454 total
includes taxes & fees
23 Aug - 24 Aug
Fireplace, Wraparound Deck, & WiFi at Chalet Cabin
Terrace/patio

8. Stone chalet w/ views & hot tub

Stone chalet w/ views & hot tub
Gerrardstown
9.0 out of 10, Wonderful, (43 reviews)
"Lovely, cozy cabin. Hot tub was very relaxing. Overall a wonderful place to stay."
United States
Michael H.
The price is HK$1,095
HK$2,404 total
includes taxes & fees
7 Sept - 8 Sept
Stone chalet w/ views & hot tub
Smart TV, fireplace

9. Secluded Cabin a Stone's Throw From the A.T.!

Secluded Cabin a Stone's Throw From the A.T.!
Harpers Ferry
10.0 out of 10, Exceptional, (42 reviews)
"We had a great stay!"
United States
Olivia T.
The price is HK$784
HK$3,106 total
includes taxes & fees
26 Aug - 27 Aug
Secluded Cabin a Stone's Throw From the A.T.!
Dining

10. Family & Pet Friendly Mountain Cabin~ Steam Shower~ 5 minutes from lake!

Family & Pet Friendly Mountain Cabin~ Steam Shower~ 5 minutes from lake!
Harpers Ferry
10.0 out of 10, Exceptional, (101 reviews)
"Great property, host was very communicative!"
United States
Lizzy H.
The price is HK$1,242
HK$2,769 total
includes taxes & fees
24 Aug - 25 Aug
Family & Pet Friendly Mountain Cabin~ Steam Shower~ 5 minutes from lake!
Smart TV, fireplace, ping pong

11. Blue Ridge Getaway - Sunset Views, A.T. Access

Blue Ridge Getaway - Sunset Views, A.T. Access
Harpers Ferry
9.8 out of 10, Exceptional, (75 reviews)
"This was an absolutely amazing stay. Beautiful location, extremely comfortable. Well stocked kitchen. Wonderful hot tub. Perfection for a getaway."
United States
Andrew L.
The price is HK$784
HK$2,831 total
includes taxes & fees
2 Sept - 3 Sept
Blue Ridge Getaway - Sunset Views, A.T. Access
Property grounds

12. Cabin at the Gap | You Won't Believe the View!

Cabin at the Gap | You Won't Believe the View!
Harpers Ferry
The price is HK$784
HK$2,705 total
includes taxes & fees
26 Aug - 27 Aug
Cabin at the Gap | You Won't Believe the View!
Outdoor dining

13. Mountain Lake Retreat of Harpers Ferry; Hot Tub-Fenced Yard-Firepit-Winery-Beach

Mountain Lake Retreat of Harpers Ferry; Hot Tub-Fenced Yard-Firepit-Winery-Beach
Harpers Ferry
9.8 out of 10, Exceptional, (9 reviews)
"Had a wonderful stay here. Shaun was an excellent host with easy communication. Peaceful location with a lake! Convenient to Harper’s Ferry. "
United States
Liz P.
The price is HK$667
HK$2,374 total
includes taxes & fees
13 Sept - 14 Sept
Mountain Lake Retreat of Harpers Ferry; Hot Tub-Fenced Yard-Firepit-Winery-Beach
Terrace/patio

14. Hot Tub, Fire Pit, Deck, Grill, WiFi, Dog-Friendly

Hot Tub, Fire Pit, Deck, Grill, WiFi, Dog-Friendly
Gerrardstown
9.0 out of 10, Wonderful, (12 reviews)
"We had a fabulous time and highly recommend this rental."
United States
Amber H.
Hot Tub, Fire Pit, Deck, Grill, WiFi, Dog-Friendly
Terrace/patio

15. Woodsy Retreat with a Hot Tub and Seasonal Views!

Woodsy Retreat with a Hot Tub and Seasonal Views!
Harpers Ferry
9.8 out of 10, Exceptional, (26 reviews)
"Great house. Comfortable beds, had everything we needed. Loved the hot tube and wood burner. "
United States
Amy P.
The price is HK$784
HK$2,705 total
includes taxes & fees
2 Sept - 3 Sept
Woodsy Retreat with a Hot Tub and Seasonal Views!
Terrace/patio

16. Peaceful mountain cabin in charming Berryville VA - next to river and brewery

Peaceful mountain cabin in charming Berryville VA - next to river and brewery
Berryville
10.0 out of 10, Exceptional, (2 reviews)
"Loved the place, the log cabin has the old world charm and beautiful settings. "
United States
Anonymous traveller
The price is HK$588
HK$1,929 total
includes taxes & fees
26 Aug - 27 Aug
Peaceful mountain cabin in charming Berryville VA - next to river and brewery
Terrace/patio

17. Forest 2BR chalet w/ hot tub & backyard

Forest 2BR chalet w/ hot tub & backyard
Gerrardstown
9.6 out of 10, Exceptional, (5 reviews)
"Just an overnight stay. On our way back home from northern New York. The place was nice. It is peaceful sitting on the deck. The check in process was a little tedious with various emails and downloads required. The Backstep is a little sketchy. Be careful walking in. Overall the place was nice"
United States
John Z.
The price is HK$1,291
HK$2,633 total
includes taxes & fees
24 Aug - 25 Aug
Forest 2BR chalet w/ hot tub & backyard
Dining

18. Log Cabin w/ Hot Tub & Waterfront Patio!

Log Cabin w/ Hot Tub & Waterfront Patio!
Harpers Ferry
9.6 out of 10, Exceptional, (25 reviews)
"Excellent property!"
United States
Michelle R.
The price is HK$1,278
HK$3,504 total
includes taxes & fees
27 Aug - 28 Aug
Log Cabin w/ Hot Tub & Waterfront Patio!
Smart TV, fireplace

19. Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!

Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!
Harpers Ferry
10.0 out of 10, Exceptional, (9 reviews)
"Welcoming host, great place!"
United States
Amanda M.
The price is HK$1,059
HK$2,941 total
includes taxes & fees
25 Aug - 26 Aug
Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!
Private kitchen

20. New 4br Townhome Near Harpers Ferry 4 Bedroom Townhouse

New 4br Townhome Near Harpers Ferry 4 Bedroom Townhouse
3.0 star property
Charles Town
The price is HK$1,572
HK$3,462 total
includes taxes & fees
31 Aug - 1 Sept
New 4br Townhome Near Harpers Ferry 4 Bedroom Townhouse
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Middleway Hotel Reviews

The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel

10/10 Excellent
"It's really the Only place to stay in Winchester. It's historic , charming, clean, and perfect. Walk to almost anywhere you like. Bar and restaraunt are excellant."
Ron 1-night trip
Posted 1 hour ago
The George Washington Hotel, A Wyndham Grand Hotel

Find out more about Middleway

Search for holiday rentals in Middleway on Expedia! You can easily find your home rentals, villas, holiday apartments in Middleway using one of the methods below:

  • View our selection of featured holiday rentals in Middleway
  • Use the map to find apartments and other holiday homes in the Middleway neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Middleway while they last

Look no further and take a look at our great range of rental properties in Middleway!

Frequently asked questions

Are there holiday rentals in Middleway?

Yes, there are holiday rentals close to the most popular sights in Middleway, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Middleway has to offer?

Family-friendly, thoughtfully modernized, historic home in Harpers Ferry.: This holiday home rental outside of Middleway offers a patio, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

What’s there to see and do in Middleway?

Explore the area and family-friendly sights such as For the Kids, By George Children's Museum, or get out into nature at a spot like Mackintosh Fruit Farm. Summit Point Motorsports Park and Old Opera House are a couple of places you'll find in the wider area.

What’s a holiday rental in Middleway like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Middleway. Holiday rentals feature amenities like laundry facilities and kitchens so you'll have all the comforts of home. If you're concerned about a sanitised environment, holiday rentals can offer a sense of seclusion away from shared hotel lifts and busy lobbies while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental a great choice for family gatherings.